5 Traits of the Worst Bosses

Michelle Benjamin, CEO and founder of Benjamin Enterprises with offices in New York, North Carolina, and Washington, DC, has spent nearly 30 years in the business of helping companies improve their management culture. Her spinoff TalentReady specifically grooms middle managers for leadership positions as they climb the ranks. She has some specific insights into what makes someone a bad boss. Fundamentally, she says, a poor leader is someone who “does not prepare their business for today’s challenges or tomorrow’s opportunities.”

The ways bad bosses do that are many, as are the damages to a business’s prospects. Some companies seem to be productive in spite of a bad boss’s shortcomings, but according to Benjamin’s experience, with truly great management the same businesses could really thrive.

Here are five traits of a boss who can make employees miserable and hamper a business’s chances of success.

1. Arrogant. “Bad bosses put themselves above the team and create a culture where it’s ‘me or us in management against them,’” Benjamin says. “I’ve worked with clients where the hallmark of the company is to recognize who’s the boss, where there is a separation of ‘us’ from ‘them.’”

Benjamin says when leadership is arrogant, there also tends to be a difference between the public agenda and the “behind-closed-door agenda.” Having a hidden agenda, she says, usurps team spirit. “It usually comes from a place of management wanting to protect their knowledge or power: ‘I know more than you and I’m not going to share,’” she says. “It serves no purpose and it’s a complete waste of time.”

2. Opaque. It’s not a new idea that transparency in management can instill trust and enable an organization to run better. But that wisdom hasn’t trickled down to many bad bosses. Benjamin points to workplaces where workers in cubicles next to each other send emails instead of speaking. “They’re protecting their backs by documenting correspondence,” Benjamin says. “They’re afraid that if they don’t document something they’ll be the fall guy. That’s the result of a lack of transparency; it’s extremely defeating.”

3. Taciturn. Similarly, bad bosses minimize the threats to a business unit, and don’t share information about threats with the team, Benjamin says. That prevents people from adding value by participating in the problem-solving process. She encourages managers to communicate about problems openly: “Say, ‘this is what I’m seeing, and this is what I want to see happen.’ And hold the team accountable.” Benjamin says just doing this creates openness and dispels barriers. “It opens up a whole new dialog.” 4. Undisciplined. Bad bosses have poor delegation skills and they don’t manage the team. For instance, Benjamin points to what she calls drive-by delegation. “They see someone at the water cooler and say, ‘I’ve been thinking about this, I’d like you to do this,’ but they don’t look back until two weeks later when the project is going in the wrong direction.” Instead, Benjamin says, a good manager would say, “Let’s sit down and let me give you examples of what I expect this project to look like and what it will look like for you to meet my expectations. Also, let me show you what I don’t want.”

To be sure, Benjamin notes, zooming in on small details and taking time to explain expectations is not micromanagement, but the opposite: “You’re making sure that what you have asked or delegated is meeting your expectations. It takes discipline.”5. Detached. Benjamin says that a good boss truly cares about employees, and that’s not just some warm-and-fuzzy philosophy. “To delegate and manage well you’ve got to know the strengths of your people, and the only way is to get to know them.” It takes time and good listening skills to know each team member’s strengths, skills, and skill gaps, she says. But with those insights, a great boss can (and is willing to) coach people to meet the expectations of the business or business unit.

Says Benjamin, “Listening to your team helps create a culture of high expectations; that’s the reason for showing the example of what you’re looking for: you want it to meet that level of satisfaction.”

Can a bad boss learn to be a good boss? “People can learn those skills, but it requires a deep desire,” Benjamin says. “I believe it can be done.” The key, she says, is “don’t drink your own Kool-Aid; if you’re the boss, you must have the vulnerability to recognize you have weaknesses and seek ways to change. You can’t do that with arrogance.”